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Volumn 6, Issue 13, 2004, Pages 2165-2168

Thioglycuronides: Synthesis and application in the assembly of acidic oligosaccharides

Author keywords

[No Author keywords available]

Indexed keywords

GLUCURONIC ACID; OLIGOSACCHARIDE;

EID: 3142777138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049380+     Document Type: Article
Times cited : (139)

References (25)
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    • (a) For a review on the use of thioglycosides as glycosyl donors, see: Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
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    • Garegg, P.J.1
  • 5
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    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1597-1600
    • Nakano, T.1    Ito, Y.2    Ogawa, T.3
  • 6
    • 0027641586 scopus 로고
    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1993) Carbohydr. Res. , vol.246 , pp. 161-172
    • Nilsson, M.1    Svahn, C.-M.2    Westman, J.3
  • 7
    • 0026713471 scopus 로고
    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1993) Tetrahedron Lett. , vol.33 , pp. 5099-5102
    • Goto, F.1    Ogawa, T.2
  • 8
    • 0028957029 scopus 로고
    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1995) J. Org. Chem. , vol.60 , pp. 2200-2204
    • Garegg, P.J.1    Olsson, L.2    Oscarson, S.3
  • 9
    • 0031021254 scopus 로고    scopus 로고
    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 241-244
    • Magaud, D.1    Grandjean, C.2    Doutheau, A.3    Anker, D.4    Shevchik, V.5    Cotte-Pattat, N.6    Robert-Baudouy, J.7
  • 10
    • 0032473815 scopus 로고    scopus 로고
    • The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1889-1892
    • Allanson, N.M.1    Liu, D.2    Chi, F.3    Jain, R.K.4    Chen, A.5    Ghosh, M.6    Hong, L.7    Sofia, M.J.8
  • 19
    • 0033534598 scopus 로고    scopus 로고
    • See also ref 9
    • Use of high concentrations of water and 2 equiv of BAIB facilitates the conversion of the aldehyde into the respective carboxylic acid: Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1999, 64, 293-295. See also ref 9.
    • (1999) J. Org. Chem. , vol.64 , pp. 293-295
    • Epp, J.B.1    Widlanski, T.S.2
  • 21
    • 3142780644 scopus 로고    scopus 로고
    • note
    • Activation of the donor for 5 min at -60°C revealed incomplete activation of the donor glycoside. We therefore started the activation at -60°C and gradually warmed the reaction mixture to -40°C within 15 min (see also ref 7).
  • 25
    • 3142751202 scopus 로고    scopus 로고
    • note
    • 2, p-TsOH, acetone; (2) TBDMSC1, imidazole, DCM, 0°C; (3) BzCl, pyridine, 0°C; and (4) TBAF, AcOH in THF (62% over four steps).


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